


A Sleepover of Sorts

by poyoboyo



Category: Critical Role (Web Series)
Genre: F/M
Language: English
Status: Completed
Published: 2019-07-13
Updated: 2019-07-13
Packaged: 2020-06-27 07:59:47
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,186
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19786627
Author URL: https://archiveofourown.org/users/poyoboyo/pseuds/poyoboyo
Summary: Caleb and Jester have had a lovely day in Nicodranas, but circumstances keep them in in the city for the night. With the rooms at the Lavish Chateau occupied, they have to share Jester’s room. Cute antics ensue.





	A Sleepover of Sorts

**Author's Note:**

> My work for Widojest Week day 5 prompt: There’s only one bed.  
> My first completed fic that I’ve ever written. There isn’t any outright spoilers to anything, but I’d catch up to at least episode 69 just in case. I apologize in advance for the tense being weird. I hope y’all like it!

The sun was starting to set on a lovely day in Nicodranas while a little blue tiefling and a human wizard were nearing the end of their three hour long conversation with the Ruby of the Sea. Muffled laughter rang from behind the door of the Ruby’s dressing room.

“And he ran out, pants around his ankles-“ Jester manages to say before her giggle fit starts up again. “The man was soaked to the bone,” Marion adds, barely managing to hold back her own laughter, hand placed daintily over her mouth. “I made sure the water was _really_ cold,” Jester snickers “ _it looked like a shriveled old peanut!_ ” With that, a snort came from the Ruby, causing her to turn away as she tried to compose herself. Jester shrieks with laughter, slapping her hand on her thigh repeatedly.

Caleb wasn’t fairing much better, tears brimming in his eyes as he wheezed uncontrollably, three solid minutes of laughter having sucked the air right out of him.

Jester’s stories were always the best. They were often crazy, hilarious, completely silly, or all three. It seemed to be that whenever she visited her mother, Jester picked the funniest ones in an effort to make Marion genuinely laugh. And laugh she did. For the past hour and a half.

They all settle down after a few minutes, sighing as they each managed to catch their breath. “I don’t think I ever saw him around here after that.” Jester says, wiping a stray tear from her eye. “I can’t imagine why,” Caleb chuckles, “you were so kind to him.” “I know right? _Super_ hospitable.” “Giving him a free, cooling bath and all.” “Exactly!” Jester beams at him and Caleb could feel his heart skip a beat.

It was a feeling he was all too familiar with as of late. She’d wiggle her eyebrows at him and his heart would flutter. Jester had winked at him on her way out of the lab back at the Xhorhouse and he had to take a short break from what he was doing to calm the rising blush on his cheeks. When she laughed at something he said, he practically turned into a pile of goo. Caleb was a mess around her, but did his best to hide it. This particular day, his resolve to act normal in her presence was put to the test.

It made complete sense why they had come to Nicodranas without the rest of the Nein. Tensions were growing from the war to the North and the streets were crawling with guards, making their arrival through a magical portal something that would arouse suspicion. The sudden appearance of two people would be easier to explain then that of their entire party. It also wasn’t clear what being a member of the Mighty Nein meant to the Empire as of late, however, with the influx of Crownsguard in the city, they weren’t about to risk it, both dawning disguises as soon as they arrived.

Jester and Caleb spent the whole day together, roaming around, taking in the sights, visiting shops, and even headed down to the beach on a hunt for some shells. It was the perfect…outing? The word “date” kept flashing into Caleb’s mind. But this wasn’t a date, right? Not in the romantic sense. It couldn’t be. Out of context it could be interpreted as a romantic date, yes, but they hadn’t even done anything particularly lovey-dovey...Well they did share a pastry or two, but-

“Oh goodness, would you look at time,” Marion says with a glance out the window, snapping Caleb out of his internal debate, “you two will probably be heading back soon, right?”

“Well…”Jester kicks her feet a little as she speaks, “ _technically_ we have some time till this curfew thing, ja?” She looks to him. “Ja,” he clears his throat, “ja, twenty-five minutes.” “See? That’s enough for like...two more stories.”

“Jester,” Marion says softly, causing the blue tiefling‘s eyes to sink to the floor, “you know that the guards are strict about curfew, regardless if it has been put into effect by a war or not.” “...Ja,” Jester mumbles, a slight pout formed at her lips, “we should probably get going then.”

“We don’t have to leave.” Both mother and daughter look to Caleb, igniting his anxiety as his heart pounded harder against his rib cage. “Heading back to Xhorhas at this hour might not necessarily be the best move on our part. We aren’t…” he hesitates, trying to think of a way to say this without it sounding completely terrible, “in the queen’s favor at the moment and it might be off-putting for us to arrive unannounced.” He looks to Jester, “I think we’d need to contact Mr.Thelyss to explain our whereabouts first. It’d probably be best to wait till morning for that.” She nods, “That’s a good idea. I kinda can’t cast _Sending_ anymore today anyway.”

Caleb quirks an eyebrow at her. Jester’s eyes innocently trail around the room as she plays with her hair, “I maybe, sorta, used it up talking to people...That dress we saw, you know the purple one with all the flowers, was something I thought Nott would _really_ like but I needed to make sure first, and then I needed her measurements because I wasn’t sure what size to get and...” her voice trails off.

A gentle smile grew on Caleb’s face as she spoke, focus on her unfaltering. Jester looked back at him, mouth giving in to a grin, “So ja it’d probably be best to wait on that, huh?” “Probably, ja.”

She smiled a bit wider at that, nose scrunching up a little as a result. His eyes shift over to address Marion, taking notice of her amused expression. Caleb clears his throat, “If there is an issue of space Madam Lavorre, I’m sure Jester and I can find rooms at a tavern nearby.“ “Oh nonsense Mr. Widogast,” the Ruby shook her head slightly, causing her horn jewelry to jingle, “there is always room for you here...Although, we are completely booked for the night.”

Jester shrugs, “People gotta release the tension somehow.” giggling when her mother looked to her with a knowing nod before chuckling herself.

“However,” Marion says, straightening herself a bit in her seat and crossing her legs as she shifts her eyes back to Caleb, “there is always the option of using Jester’s room for the night.”

His voice dies halfway out of his throat, leaving him silent and open mouthed like a fish gasping for water. He swallows a bit before taking another try, “I don’t-“

“Oh that’s a great idea, Mama!” Jester exclaims, bouncing a bit in her seat, “If we’re in the same room it makes it so much easier for Caleb to set up _Alarm_.” “No one is aware that there is another room back there.” Marion chimes in, watching her daughter nod enthusiastically. “ _And_ if Crownsguard come through here for a security sweep or whatever,” the cleric says as she looks over to the wizard, “we’ll be able to _Dimension Door_ out faster then if we were in different rooms!”

Half of Caleb agrees with the two of them while the rest of him tries to think of a logical way out of this, but his brain is so frazzled at the prospect of sleeping in the same room as Jester (when he could rarely look at her too long without feeling his cheeks starting to turn red) that all it could do was scream in panic. “I-”

At the sound of his voice, the Ruby turns her head to look at him, eyes gentle but calculating. He prayed his gulp wasn’t too noticeable as he addresses Jester, “Would that be ok with you?” The blue tiefling tilted her head a bit, with one eyebrow quirked and her nose scrunched up slightly by a smile, “Of course it is, Cayleb.” “You’re sure?” “Ja, I’m sure.” Jester leaned back a bit further in her seat and stretched out her legs, “Besides, we’ve slept in the same room before so it’s no big deal.”

If he had slept in the same room as Jester and he, of all people, couldn’t remember it, _that was a very big deal_. Caleb was just about to question her about it when she started to clarify, “Well...technically the _Tiny Hut_ doesn’t have walls and it’s shaped more like a bubble then a room, but it does protect us from the outside _like_ a room, so it’s _basically_ the same thing.” He releases the breath he didn’t realize he was holding into a quiet chuckle, Jester grins at him.

Marion looks from the wizard to her daughter, satisfied. “So,” she says, pausing long enough for them to shift their attention away from one another, threading her fingers together as her chin rested on her hands,“it is settled then?” With the look the Ruby was giving him, Caleb couldn’t help but feel like he had passed some sort of unspoken test.

  
“It’s kinda cool that I’ll finally get to have a sleepover in my room.” Jester fluffs her pillows absentmindedly as she sits on her bed while Caleb sets up the _Alarm_ spell and silently panics.

He had stepped out of the room for a moment so she could change for bed. In that time, he did his best to convince himself that this sleeping arrangement was something necessary for the current circumstances, nothing more nothing less. What Jester said had technically been true, they have slept near each other before as the Mighty Nein had traveled. Eight people crammed into a ten foot dome for safety did tend to overlap either purposefully or unintentionally in the midst of sleep. An entire room to just the two of them granted more leeway in the personal space department. The thought seemed to calm his nerves a bit…until Jester opened the door in a pink nightgown with white, lacy frills on the cuffs and hemline. He knew his face was flushed red without having to glance at the mirror on her vanity as he shuffled inside. _This was going to be a long night._

“I’d offer to paint your nails and stuff but-” a yawn cut her sentence short, the soft sound snapping Caleb back to the present, “I’m honestly super tired.” “Ja...ja me too.” He finishes casting the spell, sitting up on his knees and turning his head towards her, “We should get to bed then, ja?” His eyes flick up at her for a brief moment before resuming their staring contest with the floor. It wasn’t right for him to look at her like this. It felt...invasive. He felt dirty for being the only one in her presence because... _he’s him_ and _she’s her_. Jester deserves better company.

“Ja.” she yawns again, sliding up the bed and kicking her way under the comforter. He looks when he hears the rustling cease, taking a tentative glance in her direction to find that she’s engulfed in her pillows and bedsheets. Her blue face stands out among the pastel pink and white fabric, a small smile forming on her lips as she snuggles in. _Adorable_. Caleb’s face grew hot as his eyes fell again, standing up and walking to the opposite side of the bed before sinking to the floor besides it. “Goodnight Jester.” his voice a gentle mumble.

Caleb lay on the ground for a moment, eyes closed as he silently prayed to find sleep, until he heard shifting and creaking from the bed. He assumed Jester was just trying to get comfortable, but he was wrong. “Cayleb?” The closeness of her voice startles him, his eyes flying open. She leans over the edge of the bed looking directly at him, eyes a bit blurry from tiredness. “What are you doing on the floor?” Her voice is soft. “Was…” he hesitates, biting at the corner of his lip, “was this not the arrangement for tonight?”

“ _Caaaayleeb_ ,” Jester says in a weak whine as she rubbed at her eyes, “there’s like...a whole five feet of space that I’m not taking up. You don’t have to sleep on the floor.” He opens his mouth to speak but no sound comes out. _She… she wants to share the…? No...she has to be kidding._

“...Really?” She wasn’t, her head nodding slightly, “Come on up so I can turn off the light.” Caleb was sure that if it wasn’t for the dimness of the room, she would have noticed his face shifting to be as red as his hair. He gets up. Shrugging the coat off his shoulders and placing it near her bag on the floor at the foot of her bed frame. He sat on the edge of the mattress as he pulled off his boots, waiting for Jester to move back over to the opposite side of the bed. Once she was situated, he climbed in, keeping himself the farthest possible from her without his limbs falling off the side. “You’re not gonna get under the covers?” She asks sleepily. He shakes his head and cleared his throat quietly, “I feel a little hot...is all.” The answer seemed to suffice as she rolled over and cast _Thaumaturgy_ to blow out the lamp on her nightstand. “G’night Cayleb.”  
“Goodnight Jester.” He lay there, trying his best to ignore the sound of his heart pounding in his ears and find any modicum of sleep.

  
Three hours in and his eyes would not shut, staring up at the ceiling with his hands clasped together on his stomach. _Come on you idiot, just close your eyes. How are you going to be coherent enough to cast_ Teleport _if you don’t rest?_ His pulse may have calmed down but his mind had been racing through the past day on repeat, over analyzing everything that had happened. “...Cayleb?” The sound of Jester speaking dragged him out of his own head in an instant, startling him a bit in the process.

“Are you awake?” Her voice is slightly rough from sleep. “Ja,” he rubs at his face with one hand, “ja. I...I can’t sleep.” “Bad dream?” He hesitates. _Tell her the truth. What are you crazy? What good would that do? It would only push her away. You’re a mess._ “More like a...pleasant memory that I’m trying to discern as a dream or not.” _Coward_. He frowns at his thoughts, shifting his full attention over to her. “Did you have a bad dream?”

“The dream wasn’t really _bad_ ,” she rolls over to face him, moving closer in the process and causing Caleb’s jaw to clench, “it was just weird. Not like my dreams aren’t normally weird or anything, but this one just didn’t sit right with me, you know?” He nods. “Have you had ones like those?” “Ja,” Caleb clears his throat, “I...once dreamt I couldn’t read anymore.” “Really?” “Ja. I tried but nothing I looked at made any sense and my magic wasn’t working. It was in a big library too.” “That sounds like a nightmare Cayleb.” “Ja,” he chuckles a bit, “it kind of was.” She giggles and he relishes in the sweet song, a crooked smile growing on his face. “My dream seems a lettle silly now.” “I’m sure it’s not, but you don’t have to share if you don’t want to Jester.” “ _Well_ ,” she shifts under the blankets, her tail moving around as her leg advanced further to his side of the bed, “there was this giant dog that kinda looked like Nugget and also was a doughnut for some reason. He was hungry and he was whining for me to feed him and stuff, but all I had _was_ doughnuts. And I couldn’t _feed_ him doughnuts cause that would be _wrong_ , but he kept crying and he sort of started to sound like Pumat and I just woke up.” “I-...that sounds mildly terrifying. Definitely weird.” “It was pretty weird, ja.” “Ja.”

There’s a pause as they both lie there in silence. “You know…” Jester pipes up, twiddling her thumbs close to her face, “my mama and I used to play this game when I couldn’t sleep.” She glances up at him as his eyes find hers, her hair framing her face and eyes catching the dim moonlight seeping in from the window behind him. Caleb is positive the blush on his cheeks has returned with full force.

“What was it?” he asks, voice sounding dried out. He swallows. “We’d take turns saying one word each and make up a story. So like,” she thought for a moment, “it’d go something like this: I. Went. To. The. Park. To. Find. Some. Pet. Unicorns.” The corner of his mouth quirks up in a crooked smile. “Or we’d do funny ones like: The. Old. Man. Tripped. Over. His. Box. Of. Dildos.” He snickered, making her smile. “So...are you up for it?” “I’ll give it a shot, ja.” “Awesome.”

  
They played and laughed for most of an hour, Jester occasionally batting at Caleb’s arm playfully whenever he thought of a really good ending word. They had all but closed the space between themselves since he had almost rolled off the bed from laughing too hard and she insisted he moved more towards the middle. They were now face to face.

He could tell that Jester was starting to drift off, all the giggling having tired her out. Her answers were getting softer as her head sunk into the pillow. “One last one.” she mumbles after he suggested they both try to sleep again, “Please, Caleb?” “Alright, alright, one more.” he says softly, a tender smile on his face. “It’s your go, Blueberry.” She hums either in acknowledgement or thought.   
“The.”   
“Cat.”   
“Said.”   
“To.”   
“The.”   
“Dog.”  
There’s a touch of silence and he thinks she might have finally gone under.  
“I” she whispers.  
“Love.”   
“You.”  
“Jester.” His world shifts and the air is sucked out of his lungs at the realization of what he just said. _Oh no. **No, no, no, no, no. You didn’t. You complete idiot. Now she knows and-**_

“Yes, Cayleb?” He freezes. _She’s...she’s asking a question?... She thought you were just saying her name, say something moron!_ “I-I think I’m done for the night. With the game, I mean. I’m...I’m beat.” She hums again, her eyes shut, “Ok…” her voice sounds like she’s already dreaming “Goodnight Jester.” He turns over, hands at his face, hoping they’d be able to put out the burning of his cheeks as if they were a regular fire.

“G’night...Love you too.”

His heart stops, head turning to look at her. Her eyes are shut, with her chest rising and falling slowly as she breathes. Asleep. Caleb turns back over, his face doing a spot on impression of a tomato. Jester loves me. Jester. Loves. Me. These three words are the only thought that echoes through his mind and for a good while, his doubts are gone. All he feels is joy. Caleb falls asleep grinning.


End file.
